2-Bromoethanol → HCID 86681713, compound

HRID 571305Notes

Reaction equation

[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:9]2=[O:24])(=[O:4])=[O:3].C([O-])([O-])=O.[K+].[K+].Br[CH2:32][CH2:33][OH:34]>C(#N)C>[OH:34][CH2:33][CH2:32][N:5]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([CH2:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C:9]2=[O:24])[S:2]([CH3:1])(=[O:3])=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirred solution of tert-butyl 2-(5-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (1 g, 2.82 mmol) (prepared in an analogous manner as previously described in Example 34, Scheme 34, Steps 1, 2, 3) in acetonitrile (15 ml), K2CO3 (0.585 g, 4.23 mmol) and 2-bromoethanol (0.500 ml, 7.05 mmol) were added, and the reaction was heated under MW irradiation at 110° C. for 3 hours. The insoluble inorganic salts were filtered off, and the filtrate was evaporated to dryness. The resulting crude tert-butyl 2-(5-(N-(2-hydroxyethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (1.12 g, 2.81 mmol, 100% yield MS/ESI+ not detectable [MH]+) was used without further purification.

Workup

filtrationThe insoluble inorganic salts were filtered off
customthe filtrate was evaporated to dryness
customThe resulting crude tert-butyl 2-(5-(N-(2-hydroxyethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (1.12 g, 2.81 mmol, 100% yield MS/ESI+ not detectable [MH]+) was used without further purification

Sources & evidence

ORD record: ord-5e91d6f2d6bc4c93af2aaa1464f4d85e
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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